Stereoselective aldol reactions using pseudo C2 symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

Yuta Inoue; Takahiro Hatayama; Tomoko Kawasaki-Takasuka; Tomohiro Agou; Toshio Kubota; Takashi Yamazaki

doi:10.1039/c8cc05458d

Stereoselective aldol reactions using pseudo C₂ symmetric 1-benzyl-4-(trifluoromethyl)piperidine-2,6-dione

Chem Commun (Camb). 2018 Sep 14;54(71):9913-9916. doi: 10.1039/c8cc05458d. Epub 2018 Aug 20.

Authors

Yuta Inoue¹, Takahiro Hatayama¹, Tomoko Kawasaki-Takasuka¹, Tomohiro Agou², Toshio Kubota², Takashi Yamazaki¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
² Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan.

PMID: 30123902
DOI: 10.1039/c8cc05458d

Abstract

Crossed aldol reactions of the CF₃-containing pseudo C₂ symmetric cyclic imide 3 were carried out by way of the corresponding boron bisenolate to stereoselectively furnish the desired products 4 and this procedure allowed the preferential construction of the diastereomers of the compounds previously obtained from the acyclic counterpart 1.